Synthesis of 6H-dibenzo[b,d]pyran-6-ones using the inverse electron demand Diels-Alder reaction.

@article{Pottie2011SynthesisO6,
  title={Synthesis of 6H-dibenzo[b,d]pyran-6-ones using the inverse electron demand Diels-Alder reaction.},
  author={I. Pottie and Penchal Reddy Nandaluru and Wendy L. Benoit and David O. Miller and Louise N Dawe and G. Bodwell},
  journal={The Journal of organic chemistry},
  year={2011},
  volume={76 21},
  pages={
          9015-30
        }
}
A set of coumarin-fused electron-deficient 1,3-dienes was synthesized, which differ in the nature of the electron-withdrawing group (EWG) at the terminus of the diene unit and (when EWG = CO(2)Me) the nature and position of substituents. These dienes reacted with the enamine derived from cyclopentanone and pyrrolidine to afford the corresponding cyclopenteno-fused 6H-dibenzo[b,d]pyran-6-ones, most likely via a domino inverse electron demand Diels-Alder (IEDDA)/elimination/transfer hydrogenation… Expand
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Various kinds of 6H-dibenzo[b,d]pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which theExpand
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TLDR
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A New Protocol for the Consecutive α‐ and β‐Activation of Propiolates towards Electrophiles, Involving Conjugate Addition of Tertiary Amines and Intramolecular Silyl Migration
Herein, we present a novel approach for the consecutive alpha- and beta-activation of conjugated alkynes and demonstrate the application of this methodology towards the C-C bond-forming reactions ofExpand
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